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J Biol Chem, Vol. 273, Issue 12, 6892-6899, March 20, 1998
-Oxidation of Unsaturated Fatty Acids with Odd-numbered
Double Bonds
From the Department of Chemistry, City College, City University of
New York, New York, New York 10031
The 
-oxidation of unsaturated fatty acids with
odd-numbered double bonds proceeds by reduction of the double bond
(reductase-dependent pathway) in addition to the well
established isomerization of the double bond
(isomerase-dependent pathway). The metabolic significance of the reductase-dependent pathway was assessed with
2-trans-5-cis-octadienoyl-CoA (2,5-octadienoyl-CoA) and its products, all of which are metabolites of
-linolenic acid. A kinetic evaluation of -oxidation enzymes revealed that the presence of a 5-cis double bond in the
substrate most adversely affected the activity of 3-ketoacyl-CoA
thiolase although not enough to become rate-limiting.
Concentration-dependent and time-dependent
measurements indicated that most (80%) of 2,5-octadienoyl-CoA is
metabolized via the isomerase-dependent pathway. The
reason for the greater flux through the isomerase-dependent
pathway is the higher activity of L-3-hydroxyacyl-CoA
dehydrogenase as compared with
3,2-enoyl-CoA isomerase. These two
enzymes catalyze the rate-limiting steps in the
isomerase-dependent and reductase-dependent
pathways, respectively. Once 2,5-octadienoyl-CoA is converted to
3,5-octadienoyl-CoA (perhaps fortuitously because of the presence of
3,2-enoyl-CoA isomerase), the only
effective route for its degradation is via the
reductase-dependent pathway. It is concluded that the reductase-dependent pathway assures the degradation of
3,5-dienoyl-CoA intermediates, thereby preventing the depletion of free
coenzyme A and a likely impairment of mitochondrial oxidative
function.
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